Dismiss Notice
Join Physics Forums Today!
The friendliest, high quality science and math community on the planet! Everyone who loves science is here!

Does CH3NH2 undergo resonance? Why?

  1. Mar 16, 2015 #1

    kay

    User Avatar

    And what are the conditions for resonance to take place?
     
  2. jcsd
  3. Mar 16, 2015 #2

    Quantum Defect

    User Avatar
    Homework Helper
    Gold Member

    Resonance ususally refers to the ability to draw more than one Lewis structure for a given connectivity of a molecule. It involves the sharing of multiple bonds in different ways within the framework. In the case of H3C-NH2, you have filled valence of C and N and all of the H-es, all with single bonds. The only way to draw any kind of resonance structure for this molecule would be to include some double-bonding from the lone pair of the Nitrogen to the Carbon, but this would give you pentavalent C, which is a no-no in Lewis Structures.
     
  4. Mar 17, 2015 #3

    kay

    User Avatar

    And what about CH3NO2?
     

    Attached Files:

  5. Mar 17, 2015 #4

    Quantum Defect

    User Avatar
    Homework Helper
    Gold Member

    For H3C-NO2, there is resonance in the -NO2 group, but you can't make C pentavalent. On the N, there is a formal charge of +1 and a formal charge of -1 on one of the oxygens.

    For the picture that you show: H2CCHNO2, there are more resonance structures possible, but one of these will not be particularly important.

    e.g. H2C-CH=NO2 [Each N-O bond is a single bond]
    This Lewis Structure has +1 formal charges on the end Carbon, and the Nitrogen, and -1 formal charge on each of the oxygens. Separation of many, many charges like this is something that is difficult to do -- i.e. you would need to do work to separate the many charges, so chemists would say that this is a high-energy isomer, and does not contribute much to the true picture of what the real molecule looks like. For example, the charge density on the end carbon is probably pretty close to what you would expect for a neutral carbon, and the terminal C-C bond is probably closer to what you would expect for a double bond, than a single bond as drawn above.
     
  6. Mar 18, 2015 #5

    kay

    User Avatar

    So I can always assume that whenever a resonance structure has a pentavalent carbon, it doesn't exist?
     
  7. Mar 18, 2015 #6

    Quantum Defect

    User Avatar
    Homework Helper
    Gold Member

    Octet or less only (four electron pairs as bonds/lone pairs) for elements in the first complete row (BCNOF). Five bonds (pairs of electrons) are out for these elements, including Carbon.
     
Know someone interested in this topic? Share this thread via Reddit, Google+, Twitter, or Facebook